


Cadillac, Cadillac

by lipstickkarma (Scarf_Sociopath)



Category: Supernatural
Genre: Dean - Freeform, Fluff, M/M, castiel - Freeform, highschoolAU
Language: English
Status: In-Progress
Published: 2015-04-03
Updated: 2015-09-27
Packaged: 2018-03-21 02:06:21
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 3,339
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3673494
Author URL: https://archiveofourown.org/users/Scarf_Sociopath/pseuds/lipstickkarma
Summary: <blockquote class="userstuff">
              <p>Two weeks into his senior year of high school, Dean Winchester, stereotypical straight boy extraordinaire meets Castiel Collins, a brainy bisexual born in Boston. Will Cas succeed in bringing Dean's latent homosexuality to the surface? There's only one way to find out...</p>
            </blockquote>





	1. Chapter 1

Dean smirked as he watched the gaggle of freshmen stare, confused, at their maps. He'd been in their place once, sure, but that didn't mean he couldn't enjoy their frustration.

"Mr. Winchester?" the school secretary. Dean quickly ran through a list of his offenses in the first two weeks at Austin High. Skipping English, throwing food at that annoying prick in Health-

"Mr Winchester, if you are even listening, this is a new senior. I would like you to show him around."

Dean's head snapped up. What? Oh.

The kid was was tall (though not taller than Dean), with blue eyes and mussed-up hair. Kinda cute- wait- did he just think that?

"Um, sure." The teen almost shoved his hand into the other's.

"I'm Dean." an awkward handshake ensued.

"Castiel." Wow. Growly and gravely. The secretary smiled and walked back to the main building, heels clacking against the cement.

"So Cas, where ya from?" Dean smiled. The guy looked like the type of person that Dean would like to hang out with.

"Boston." Sweet baby Jesus, that voice.

"Why'dya come all the way to Texas?" The boys walked through the front doors, air conditioning hitting them full force.

"Relatives." Short. Curt. Not looking to elaborate.

"Huh. Neat. Anyway- that's Mr. Wellington's room, teaches History. Missing the class right now actually." Dean was aware that he was rambling.

"That's...nice." Cas didn't even smile.

"Is your school supportive of homosexuality?" Dean nearly choked.

"What?" he sputtered.

"You heard me." It wasn't a question.

"Um, I guess?" Not that Dean would know. The Winchester was so far in the closet that his ass was getting frostbite.

"So, if I chose to wear some LGBT-supportive shirts I would not get sent home."

"Yeah?"

"Thank you Dean." Castiel smiled a barely discernible smile, and strolled away, leaving Dean standing stock-still in the hallway.

"How was your first day?" Dean smiled, tossling his little brother Sammy's hair. Sam ducked, and shrugged.

"What happened Sammy?"

"Nothin' important, Dean. Let it go." Dean stopped, and knelt down to reach Sam's level.

"Nothin's never nothin'." he said, adjusting the straps of his little brother's Swiss backpack.

"Some British guy named Crowley." Sam learned too much from his older brother. Dean sighed, straightening and swinging an arm around Sammy.

"Yeah, fine. Let's go home, Elsa." They resumed walking. He almost missed Cas standing a mere five feet away, smiling shyly. Dean beckoned him.

"Um, Dean, I'm sorry for how I acted earlier. I was a bit nervous." Dean held up a hand.

"It's fine dude." But internally Dean's mind was racing. Were Cas' lips always that soft and inviting and slightly shiny and- Dean realized that Cas was looking at him expectantly. He was waitong for an answer. Fuck. Ummm...

"Are you walking this way?" he blurted, " A lotta people do."

Castiel nodded, ducking his head down.   
And that's how everything started.


	2. Look, It's a Library!

**Summary for the Chapter:**

> Sam gets into an advanced program, which makes him stay until four. Dean has to walk his little bro home. Cas hangs out at the library. Guess what happens.

Dean fast-walked (scratch that- ran) to the front of the building. He had been talking to one of his professors about a homework paper...Sam would be pissed. Little bugger never liked waiting. As the rounded the corner, he managed a glance inside the library. Castiel was standing there, nose buried in a book, and looking, well, great. The sunlight from a window behind the older boy cast a perfect halo around his slim body.   
Dean hurried on before Cas could realize that Dean was gawking.

***  
"You're in what?" John Winchester repeated for what seemed like the fifth time. Sam only looked calmly at him, mimicking his father's position, fingers laced, slightly slumped over.  
"Dean won't be able to walk you home."  
"Actually, about that," John's head snapped to Dean, who had been quietly eating his pot roast, "My friend, Cas? He stays after in the library."  
"Huh," John glanced back and forth between his sons, eyebrow arching. He turned to Mary, standing at the kitchen counter. She shrugged.  
"Dean's got a good head on his shoulders. He can manage to not cause any trouble." John sighed in defeat and shrugged.  
"Make sure y'all get home by 4:15. Ya hear me?" Both boys nodded, and ran upstairs. Mary smiled at John, who managed to turn the points of his mouth upwards.  
"Sometimes I worry about those two. Can't be healthy, bein' so attached to each other." he said, standing up.  
"Oh honey, you know that it's perfectly alright. People need that kinda loyalty." She kissed John on the nose, and went to read.

"But you don't even know Cas that well! You barely talked the one time we walked together!" Sam had barraged Dean in his typical fashion when he thought that his older brother was hiding something.  
"Look, man, you wanna be in this nerd program. I'm going to make sure you get in it and excel. Got it?" Dean went into his bedroom before Sam could say anything else.  
***  
"Uh, hey, Cas?" Dean nervously paced through the doorway. Castiel swung around, and scrunched his eyebrows.  
"Dean? What are you doing here?" Dammit.  
"My brother, Sammy, he got into a elite kid next-world-genius program and he has to walk home with me, so I thought it would be cool to hang with 'til, like, four?"   
"Cool?"   
"Dammit, Cas. I'm already awkward enough about this as it is." Castiel nodded slowly, beckoned to a bookshelf, and went back to reading.


	3. Simple Dog

**Summary for the Chapter:**

> Cas gets pissed. And Dean feels bad. And I feel bad for not writing sex yet.

Dean scanned the spacious room for school gossipers, then looked back at Cas.  
"Please stop staring." Dammit.  
"I'm not staring." Castiel didn't respond to that, and flipped the page of his book. "What'cha reading?" Dean tried again.   
"Oh c'mon, don't go all silent on me, nerd."  
"Hyperbole and a Half."  
"Is that, like, a grammar book? 'Cause I gotta say man, that's pretty lame, even for y-" Dean was interrupted by Cas shoving the book in his hands.  
"Read it, dickwad." Cas hissed, clearly pissed off, "And learn proper grammar."  
"What did I say?!" Dean shouted back at him. And then he thought. And then there was dread.  
Dean left the library disgruntled. Sam could tell something was up, the little bitch, but Dean just shot him the bird and slammed the door closed.  
"You always say the dumbest things." Dean groaned, rolling on his bed. "What the fuck am I supposed to say?" he rolled up, tugging at his blonde hair.  
"Dean?"   
"Go away, Sam."  
"Do you wanna listen to Metallica."  
"No."  
"Okay, bye." Sam trudged (rather loudly) away from Dean's room.  
***  
"Cas! Cas!" Dean ran toward the other boy. "Castiel, I'. sorry. I was being stupid. I won't do it again."  
Cas turned around, expression cold, but with something flickering in the back of those sea-blue eyes.  
"Please be my friend." Castiel caved, face softening, a little smile tugging on his perfect mouth.  
"I'm sorry, too, Dean. Life's been...tough." then he perked up. "Did you read the book."  
"Yeah, a bit," Dean laughed. "I like the intro."  
Cue headtilt.  
"Y'know, 'For Scott, now what, fucker?'" Cas just gave him a blank expression. "Alright, anyway, I did love it. Almost done."   
"Tell me when you're done, I didn't check it out." A wry smile, and then the brilliant, dark-haired boy was gone.  
Poof.


	4. Phone Numbers and Lollipops

**Summary for the Chapter:**

> I'm back from the two-week hiatus!!!

“Hey.” Dean scooted into the cafeteria bench, across from Cas. The boy had a cheeseburger, which is not resemble a burger as much as it did a squashed Big Mac mixed with day-old mystery meat. Still, there were two big bites out of it. “Hello, Dean.” “So, Cas? Can I have your number?” Castiel’s head tilted. It was pretty cute. Wait- did he really just say that. “I mean, like, friends-based. I don’t want- you know what? Never mind. How were your morning classes?” “Not good. Professor Lecter made us dissect rats.” Cas shuddered. Dean patted him on the shoulder. “So did you say ‘no’ or what?" “Yes. I’m not sure my parents will be very pleased, though.” “You gotta support your beliefs, dude. It’ll be fine.” Cas nodded slowly, as if he didn’t believe Dean.

***

“Watch out!” Dean growled as some freshman rushed past him. The kid looked back in pure terror. Dean swung his head back, continuing his journey to the football field for practice. Cas was there. That was the first thing Dean noticed.  
Not the cheerleaders, not his coach.  
Cas.  
He stood and walked from the bleachers, smile widening. Dean shot a look to the other players. They were too busy watching a vid from a Clark’s phone. Probably another viral Vine. God, those were stupid. “Here.” Castiel shyly handed Dean a slip of paper. Dean took it, confused but interested. He looked up, at Castiel. The blue immediately captured his gaze. They stood like that, staring at each other until a shout came from the coach for Dean to,  
"Stop flirtin’ an’ get over here, boy!". This made them both blush, jumping away. Cas hurried back to the main building, head down.  
“Who’s that, man?”  
“Yeah, what’s with the nerd?’  
“Is he your boyfriendddddddddd?” The last came from Gabriel, a short quarterback that had a persistent sweet tooth. As of the moment, he was sucking on a lime green lollipop with a zebra design. Dean flipped him off.  
"Just some nerd with a tiny prick that does my homework for me." The others laughed, Dean trying to ignore the guilt clawing at his stomach. He glanced down at the paper. It was a phone number.  
***  
_"Is he your boyfriendddddddddd?"_ The words were echoing through Castiel's skull.  
"I want him to be," he whispered, so quiet that even he could barely discern the confession.  
Dean was super nice, letting Cas walk home with them, but, from Castiel's experience, his actions on the first had already fucked the possibility of a relationship up.  
Cas let out a heavy breath, and hurried to History.


	5. Shoes and the Boys

**Summary for the Chapter:**

> Ugh I'm sorry I haven't updated in so long. My brother came over from across the state for the summer and WE LITERALLY SPENT EVERY MINUTE OF IT TOGETHER WE EVEN SLEPT IN THE SAME ROOM LIKE WE WERE LITTLE KIDS. It was so fun. Now I miss him :((.   
>  Anyway, he wears the same shoes that Dean does in this chapter and I am the onlt one that can even hold them.   
>  This is for you, Cormac. :))

"Baby I'm preying on you tonight  
Hunt you down eat you alive  
Just like animals."  
Dances. Ugh. Castiel surveyed the room, some godawful mixture of fruit punch in his hand. Balthazar had dragged him to the school at eight o'clock, promising that a certain...someone would be there.  
At least the music was good.  
"I didn't think this was your thing, Cas."   
holyshitisthatdeanomgstaycool  
"I'm afraid that my brother convinced me to come."  
"Oh. Neat! You doing anything after th-"  
"Dean, come on!" a, very pretty, girl practically latched herself onto Dean, "We were gonna have some alone time."  
She noticed Castiel. Her eyes narrowed. And proceeded to nuzzle Dean's ear, peppering his cheek with kisses.   
"Well, I hope you guys have fun." Cas swallowed his disappointment, plastering a smile onto his face, "Use protection!"   
The girl seemed relieved, and she quickly swiveled Dean around.   
Cas left before he saw any more.  
***  
The day after the party was physical education.  
Dean had gotten dressed early, jogging laps around the gym. He and Cas had the class together, but the blue-eyed boy was still in the locker room.   
Last night was fun. At least that's what Dean was telling himself. Lisa was a good girlfriend, she cared, she was smart, but she wasn't what Dean wanted. Not anymore.   
As Dean rounded the bend, Cas came out of the room. He was dressed in a tight blue shirt, loose blue-and-orange shorts, and wow were those KD's?  
If Dean had panties, they would've dropped.  
Unconsciously, he slowed down enough so that Castiel caught up with him.   
"Hey Dean." Man, the kid hadn't been running for half a minute and he was already getting winded.   
"Hia Cas. How're you doin'?"   
"Erh, good. Could'ya slow down a bit, though?" Oh. That's why. Dean ran faster when he was nervous. He backed off the steam a bit.  
"Sorry man, I'm just hyped up." Cue headtilt from Cas, "Big game tonight, y'know? Football. Wanna come?" Wait. What.  
"Sure!" Castiel's smile was so pretty. Dean could fall in love with how his eyes crinkled in the corners. The jock realized that they were running really, really close. Like shoulder-and-hip touching close. Dean cleared his throat and moved a few inches away.  
"Nice shoes," he gestured faintly at Cas' feet, trying to change the subject. The KDs were black and silver and totally awesome.  
"Thank you, Dean. Yours are the same brand?"   
"Uh, yeah!" His were black and orange with ventilated holes in the back sides. Nobody touched them. Nobody. Not even Sam. They ran a few more laps in silence, mostly because Cas was becoming slightly pale and breathing heavily. The sounds totally did not go straight to Dean's dick. Nope.


	6. Crush Crush Crush Your Enemies

**Summary for the Chapter:**

> Bunch of stuff not really relevant to the plot happens. Jk, there is no plot.  
> TOMORROW IS MY BIRTHDAY YASSS.

Castiel was tired. His morning hadn't started well, the walk to school was cold so he had thrown on a comfy maroon sweater, but it quickly had escalated to about ninety and Cas was swimming.   
"You good, bro? Hangin' in there?" Dean's worried faces warmed Cas even more.  
"It is very hot, Dean."   
"Hey, man you could'a told me earlier. I have a spare shirt in my locker. Might be a little big but-"  
"I would appreciate that." Cas' eyes turned upwards to Dean's, and the freckled boy's legs almost turned to jello.   
***  
"Oh."  
Cas had taken off his sweater (why'd he even where it?) and was standing in front of Dean. The sweat was obvious on his lithe body.   
"What is it, Dean?" The previously mentioned physique was turning a slight pink, probably from being stared at so openly.  
"You're so..." Dean paused, "Thin."  
Inner Dean punched outer Dean in the face. Multiple times.  
"Does that bother you, Dean?"   
"Nah, dude, I guess there's a reason you didn't try out for the football team." Dean cracked an awkward smile, and had to wait for a few horrible seconds before it was returned.  
The shirt was slipped on (turquoise, Dean's favourite), with 'Soaked- Water Marathon' written across the chest. Dean realized with a start that it had 'Winchester' in big, bold print on the back.  
The guys would never let this go.  
"You and your boyfriend already sharing shirts, faggot?"   
"Fuck off, Benny, he needed a shirt. Came to school with a stupid sweater." Benny wouldn't let up, so Dean flicked his fugly hat off his fugly head. The dickwad was known as a homophobic prick.   
The second worst thing about him was that he couldn't play football for shit. God and Sweet Joseph only knew how he got on. He was a right field linebacker, too, which wasn't as impressive as Dean's (QB), but enough to grate on the boy.   
Then the dick spotted Cas, near the school, obviously looking towards the field. Waiting for practice to finish so they could walk home.   
"Oh, look there he is. He good in the sack? Maybe I could tr-" Benny didn't get through his sentence before Dean's fist met his stomach. It would've been the face, but, well, helmets.  
Benny tried to tackle Dean, but he was too fast, connecting his knee with Benny's groin. Repeatedly.   
"Break it the fuck up! What the HELL are you thinking, Winchester? And about you, Latiffe? Fucking with my best player?" Coach Wartnow's jaw was hard-set, eyes glinting.  
"Get outta my sight. Both of you are suspended from the next two games. Aiden, you're the new quarterback."   
**  
"You kicked that guy pretty hard." Cas hadn't talked for the whole time it took to get to the crosswalk on Grand.   
"Yeah, he deserved it."  
"What did he say?" Dean froze for a millisecond, eyes darting to Cas' lips.  
"Ta-Talkin' trash about Sammy, pretty much. Um, nothing to worry about. At all. Yeah." This is why Dean wasn't in drama.  
Cas didn't seem to notice though, fast-walking when the "walk" sign flashed on.   
"Wanna stop at my house? We can chill for a bit." Dean blurted out, running a hand through his hair.   
Castiel started jumping on dry leaves, "Sure! That'd be cool. 'Till 4:45?" He looked so excited, Dean chuckled a bit, and raised his head up, striding to his house.  
No one was home, so Dean and Cas sat on his couch and played Halo until four, before they both realized that they were both leaning heavily against each other, Castiel's head on Dean's shoulder.   
"Uh-" Dean started, blushing. Cas didn't say anything, a mirror expression on his face. The blue-eyed boy's eyes darted, finding a UFC: Rowdy Rousey Edition CD on the tv table.  
"You're into MMA?" his voice was a little higher than usual.  
"Yeah, um, you wanna watch 'em?" Dean was already getting up, unhooking the Playstation, turning the Apple TV to Video 1.   
"I'm afraid I don't have much knowledge in this area."  
"Oh, it'll be fine, dude. I'll explain." 

The tape started. Almost immediately, a badass-looking chick appeared, throwing punches.  
"Ronda Rousey." Dean said, with unmistakable awe in his voice. Castiel soon saw why.  
The chick was an arm collector. Most of the fights he saw were won with an armbar- one opponent cranking another's arm 90° in the wrong direction. There were cuts of training, striking with two pound weights and grappling- floor fighting, basically- and all the while, Cas watched Dean.  
The admiration on his face, slack-jawed. But it wasn't the kind of look Castiel saw when other boys looked at a "hot" girl. This was respect. And Cas wanted it to be directed towards him.  
***  
Dean scoped around the Advanced English room.  
"Are you lost?" Dean's hackles rose at the arrogant attitude of the voice. He turned, looking down to see Emily Cheddar, a bitchy genius that played cello really fucking well.   
"No, sweetie, I'm not. Where's Castiel Novak?" She seemed baffled. Good. Then she smirked.  
"I dunno, why should I tell you?"  
Dean ground his teeth, then hissed, "Because I will fuck you up if you don't. Don't play with me."  
Emily snorted.   
"You're just a brainless, egotistical jock who doesn't have any abilities other than sports."  
Dean flinched. Dammit. Her words struck one his most sensitive nerves. His mind flashed back to John Winchester looming over him, eyes flaming, ready to strike his son down with the same words.  
"Hello, Dean. Is Mouse bothering you?" Cas had appeared at his side like a guardian angel. Thank God.  
"Nah, man. Just tryin' to get to me. Can't say she's as good at verbal sparring as she is sticking that cello up her ass." Dean chuckled- forcefully- at his own words, aiming a supposedly playful look at Emily-or Mouse, according to Cas-, to find her glaring, her little face flushed. She abruptly turned and stomped off.  
"So, why did you need me, Dean?" Cas swiveled to look at Dean.  
"I wanted to give you this." Dean held out 'Hyperbole and a Half' like an offering, "It's probably late, so I'm sorry about that, but I had to reread it a few times."  
"Did you like it?" Cas' eyes sparkled. Dean could get addicted to that. He nodded an enthusiastic 'yes'.  
Then the period bell rang. Dean groaned.   
"Want to skip?" Dean cast a baffled look at Cas. Did the perfect nerd boy just-  
"Uh, sure."

"Neat! Where do we go?" 

The boys walked halfway down the hallway, and made a swift turn into the bathroom, heading towards the handicapped stall, because it was the biggest.  
"Dean?"  
"Yeah, Cas?" They had been sitting for about two minutes, Cas doodling in his notebook, Dean watching.  
"What if somebody with a disability comes in?  
"Then we can just crawl to the other stall, dude. Don't sweat it." Castiel nodded, head bowing down, focusing again on the blue-and black ink, highly detailed bee he was drawing.  
"Whoa, man. Wasn't that just circles? How?"   
Cas realized that Dean had the same tone of voice as when they were watching UFC together. He smiled.  
"It's practice, and liking what you're drawing."  
"You like bees." It wasn't a question.  
"They're very important to the environment. If bees were to disappear, eventually, so would humanity."  
"Huh." Dean hadn't known that. He didn't think he was the type to find those types of facts interesting, but maybe it was how Cas said it, with affection and knowledge.   
***


End file.
